


The Pickup, the Hookup, the Wager, and the Spoon

by 9091



Category: Supernatural
Genre: Bossy Dean Winchester, Condoms, Cunnilingus, Dirty Talk, F/M, Multiple Orgasms, Orgasm Denial, Originally Posted on Tumblr, Restraints, Smut, Tumblr, just a tiny bit of fluff
Language: English
Status: Completed
Published: 2019-02-27
Updated: 2019-02-27
Packaged: 2019-11-06 17:30:46
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 7,646
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17944073
Author URL: https://archiveofourown.org/users/9091/pseuds/9091
Summary: Oops, lost my Dean/Reader cherry, after falling in with abadgoodcrowd.





	1. The Pickup

**Author's Note:**

> Oops, lost my Dean/Reader cherry, after falling in with a ~~bad~~ _good_ crowd.

**Summary for the Chapter:**

> You're having a drink at your favorite bar. Then, Led Zeppelin music fills the place. There's a man standing next to you in a flannel shirt. Guess who it is.

You’re having a whiskey at the bar, trying to blow off some steam, when he moves into the space next to you, kind of resting one hip on the stool, but mostly standing. You tilt your face toward him, interested, wishing he was looking in your direction.

You like this bar because it’s not your home turf. It’s a bit farther into downtown than most of your friends are willing to travel, and you don’t tell them where you go. You used to have a neighborhood place… until your boss decided he liked it, too.

Fuck. That.

But here, you can be a stranger. Cold or warm, flirtatious or quiet, as you see fit. Speaking of flirtatious, this dude who just walked up has good taste. He just ordered a glass of what you’re drinking, without any of that, “I’ll have what she’s having” BS. Wait, do guys even do that, or is it just the movies?

It seems weird, but you like the way he stands, the sort of forceful way he claims his space. His shoulders are broad, his jeans faded and ripped, his light brown hair is spiky in the front, but not in that finicky “obsessed with hair products” way. He smells nice, like a fresh shower, and… something else… the smell of someone who’s been outside in the sun, maybe working. That warm “fresh air and hot asphalt” smell. You can only see some of the side of his face, but it’s promising.

You swirl the ice around in your drink, and consider that maybe today you’re playful rather than cold. Or maybe it’s the sudden influx of Led Zeppelin from the jukebox. You jump in with both feet, hoping to score a better look at him. “Hey, flannel shirt?”

He continues to drink. For a disappointing second, you think maybe he didn’t hear you, but he looks down at his shirt to check, turns toward you, and…

 _Abort mission! He's too hot, we've made a mistake_!

Later, you think to yourself that if you had a notebook and a pen, you could’ve captured everything right about him, but in the moment, he’s just an overwhelming barrage of green eyes, laugh lines, a spray of light freckles, and whiskey-slick lips.

 _Act like you didn't say anything_ , is your brain’s oh-so-helpful suggestion.

Well, shit. Nothing to do but roll with it. You take a deep breath. “Cheesiest pick-up line you’ve ever used. Go.”

He blinks those gorgeous eyes at you, processing it, and then one corner of his mouth lifts. “Told a couple of girls I was a talent scout for a reality show.”

His voice. Sweet mercy. Your brain tunes up the alarms again. If you’d ever had the really expensive stuff, you’d bet it tastes the way he sounds.

He turns away to tap his finger on his empty glass; he has the bartender’s undivided attention. As he turns back to you, you realize you’re not any better prepared than before.

“How did that work as a pick-up line?” You’re honestly curious.

“Looking for, uh, special skills and abilities.” He laughs a little to himself and even this is sexy. “You know, tie a cherry stem in a knot with your tongue, crazy positions, double-jointed hips…”

You shake your head, smiling. “And this worked on somebody?”

Slyly, he holds up two fingers. You get an involuntary jolt, imagining his fingers wrapped around your wrists.

You blink at him. “ _Two_? No way. Two different girls?”

He grins. “Well, two girls, but just the one time.”

“What, on the same night?”

His whiskey glass is full again, and now, so is yours. You didn’t notice.

He takes a drink, then licks his lips, breaking into a smile that borders on public indecency. “At the same time, so… yeah.”

The mental image that floods your brain –- naked skin grinding desperately on his –- is like an electric shock. You wonder if he hears it in the thickness of your voice when you say, “I don’t know if a pickup line that accomplished… well, _that_ … counts as ‘cheesiest’ to be honest.”

His eyebrows are _up_ now, and his face takes on this lazy, languid sort of look. “You oughtta hear one of my good ones.”

You choke on whiskey. You try to recover, but it’s too late. “Umm, okay… um… I’m gonna go over there, by the jukebox, and I’d like you to hit me with one of your good pickup lines.”

He leans down (he smells so good) and whispers low into your ear, “Do I really need to?”

You clear your throat awkwardly, and when you can talk again, your voice cracks like a teenage boy’s. “Indulge me… what would you have said?”

Even closer now, you feel his warm breath on your neck. “Sometimes, a woman gets good and wound up, and she gets a leg cramp when she gets off, because she was so tensed up, and then she has the release… too much good stuff happening at one time. You know?”

Maybe you don’t know.

He licked his lip, mock contemplative. “Well, I think I figured out a way to untangle that muscle when it happens. I just need to perfect the technique.”

You blink at him, feeling your whiskey, as he pulls away. “That was kinda cheesy.”

He grins, a laugh low in his throat. “Wanna get outta here?”

Downing the rest of your glass, you grab your purse, “Hell, yes.”

“Dean,” he says, putting money on the bar, for your drink as well as his, waving your hand away when you start to protest. “My name is Dean.”

“My name is Y/N,” you say breathlessly. “Dean, do you feel like this whole conversation might have happened backwards?”

He laughs, putting one hand on your lower back to help guide you through the crowd.


	2. The Hookup

**Summary for the Chapter:**

> You get a nice hotel room and Dean Winchester tells you about his special rule regarding the ratio of his orgasms to yours.

“Let’s take your car,” he says.

You would’ve insisted, if he hadn’t suggested it. 

He stops off at his car (a babied classic Chevrolet that makes you like him even more) and gets something out of the glove compartment and sends someone a text.

You’re thinking about how long it’s been since your last hookup, but none of them were like this, a stone-cold stranger who picked you up in a bar. They were people you knew casually through others, and you remember the awkward minutes leading up to the hook-up and dread them. 

Dean slides into the passenger seat, suddenly more real here than he was in the bar. You notice more about him. The “swagger” he moves with isn’t a put-on; he actually moves like that. His torso is thick and he has a worker’s hands. But mostly? No awkward minutes. He’s smiling and at ease, and it puts you at ease. 

You bring up a list of hotels on your GPS. You’re downtown, so there’s lots of options, but… “Should I be searching for an hourly place?”

He makes an offended noise, wide-eyed, mock-hurt. “Only if you want to rush me, Y/N.”

 _Oh_. You blush furiously, but you like the way your name sounds in his mouth. Hey, maybe you’ll hear it again a few more times.

With any other hookup you’d had, there’s that almost shy and prudish build up on the ride over, like two people pretending they’re not nervous, not about to fuck like animals, but Dean’s attitude is infectious: “We’re gonna have some fun.”

Then again, you’re not sure you were as horny then as you are right now. 

That’s when you decide to pick the closest hotel, the one that’s practically down the street. 

Dean does the checking in, and collects the key card for the room. He’s looking all around. “Nice place. When the key’s on a card, that’s how you know.” He smiles wide. “You think there’s room service? I bet there’s room service.”

You can’t help but smile as you watch him. The thought of room service has somehow turned this big 30-something man into a little boy. 

Dean slides the key card and turns the handle. He stands aside to let you into the room first, his hand on the small of your back again. 

As you’re idly wondering if you should shower again, or get ready for him somehow, the door clicks shut behind you. He puts a hand into your hair, his rough fingers grazing your neck, and kisses you on the mouth. He still tastes like your favorite whiskey. His mouth is warm and soft, and you let yourself get wrapped up in the kiss. 

His is a practiced mouth. There’s no awkward “let’s take off our clothes”, because as his kisses grow deeper and hotter, you’re desperately trying to remove your own pants. It’s like he’s using up the part of your brain that can do anything else but kiss him, because you’re not having any luck. He pauses between kisses for breath, and to help you, fingers nimbly loosening your belt buckle and then his own. As he kisses you, he has an absolutely devilish grin. 

“W-what?” 

He winks, and looks over your shoulder. “Just thinkin’ about all the uses for a belt.” 

You follow his gaze to the bed’s ornate headboard and blush again. 

He shrugs out of his flannel shirt, and pauses to yank his t-shirt over his head, messing up his hair a little in the process. Then he works on the buttons of your shirt. His hands are not as clumsy as you thought they might be, and looking at all the bare skin of him (is that _more_ freckles on his shoulders?) gets you hotter. 

Instead of taking you over to the bed, he easily hitches your legs up around his waist and pulls you into an overstuffed chair onto his lap. You’re absently aware that your underwear is still on, but more aware of how hard he is in his boxers.

You playfully grind on him a little and he groans. “What’d I say about rushin’ me?” Dean’s voice has taken on a little bossiness now that he has you where he wants you. He runs a finger down the closures on the front of your bra. “Aw, I love when they open from the front.”

You start to unfasten it, but he stops you, pulling you close and putting his face in your cleavage. You wonder if he’s going to try to open your bra with his teeth or something when you feel his hands disappear from around your waist. Suddenly, he’s lazily rubbing his thumb over each of your nipples through the lacy fabric. You make a desperate little squeak without meaning to, and he laughs. 

You can’t help but laugh with him, pulling away, unfastening the bra quickly at first, until you realize that he’s growing harder against you. He likes a little show, huh? You take pains with the last few hooks, playing it up, enjoying his rapt attention, grinding on him a little bit more. 

As your breasts are exposed to the air, hard nipples getting harder, he moans and shifts in the chair, blocking some of the threat of your impromptu lap dances. You start to reposition yourself with a pout, but he takes your breasts in his hands and his thumbs are even more deadly now. You’d say your nipples have never been this hard in your life, but that’s before he licks each one, and then gently exhales across them. 

Can he tell how wet that just made you? You shift around yourself, dizzy. You can’t believe you felt awkward for even a minute, not when you feel like this. 

He has a throaty laugh, “Oh, I think you liked that a lot.” He pauses to suck gently on one nipple and then the other. “You know…” Again with the sucking. “I read somewhere…” And again. “Some women can get off…” And again. “Just from this. The nerves are connected or something? I forget.”

“Don’t talk with your mouth full, it’s rude.” You try to sound more sarcastic than turned on. You fail. 

You feel the throaty laugh against your breasts now, as he sucks one, and then the other, looking up occasionally to watch your face. You can’t take your eyes off his talented mouth, on how focused he is, on how he licks up from under so he can watch you. With his fingers digging into your hips, he drags his lower lip slowly up your right nipple before sucking it harder than before. 

You moan as all your muscles seize and release. You’re so wet now that your lacy panties feel stuck to you. 

“I knew it,” he said smugly. 

It feels like you’re fighting to hold your arms up. You grind desperately on his cock again, softly scraping the hard bulge with your fingernails. “Fuck me.”

“Ohhh, did I not tell you about my rule? I got a few, but the big one is: six to one ratio. Or, whenever you can’t actually speak anymore.” He raises up out of the chair with a grunt, putting you right in riding position if it weren’t for his damn tight boxers. 

He playfully drops you on the huge bed. “The not talking thing is for when I lose count, which I do. A lot.” He grabs your ankles and drags your ass down to the edge of the bed. He kneels down and pushes your thighs apart. That damn thumb of his starts rubbing you through your panties, parting you, feeling how wet you are. 

You make another stab at composure. “Should’ve led with that… would’ve gotten here sooner…”

“Should’ve led with this?” He pushes your panties to the side and slicks his thumb over your clit and down to your pussy, then back again, a lazy little round trip. “In front of everyone at the bar?”

Before you can take it back, you suck in your breath at the image, and clench around his thumb. Now he switches to two fingers, going inside you just far enough to make a little “c'mere” gesture. 

He laughs again (you’re giving him a lot to be smug about). Shifting around, he gets up to lie beside you, so that you’re half spooned up. He reaches down, his two fingers continuing their lazy work. You have your knees drawn up so you can meet him faster, but he keeps the strokes infuriatingly slow. With his mouth next to your ear, he says, “How long do you think I could do this back at the bar before someone called the police?”

You tense around his fingers again, and when you can open your eyes enough to look at him, he’s grinning from ear to ear. “Y/N, you dirty girl. Maybe if we were sitting at a table? I could finger you just like this.” His voice drops to a whisper. “But you’d have to be so quiet. Here you can scream. You can make people in the next room jealous. You can make housekeeping blush.” He dips his fingers in farther, and you’re thankful for those rough, worn hands. “Did I hang the ‘do not disturb’ thing on the door?” He thrust both fingers into you up to the last knuckle. “Guess we’ll find out.”

You think of someone walking in and seeing your shaky legs spread so wide, hips bucking hungrily at his hand, and you lose it. You fuck his fingers hard and fast, crying out. He leans down and sucks your nipple, hard. You cry out again, as all your muscles tighten, then loosen around him. 

You can tell he’s smiling just by the sound of his voice. “Was that 1 or 2? See what I mean about losing count?”

You manage to hold up three fingers, gesturing inarticulately at the overstuffed chair.

“You count the one in the chair? That was just warming up.”

“Oh, god,” you moan, grabbing at the sheets, riding the final waves of pleasure. 

He gets back on the floor now, kneeling, pulling you back toward the edge from where you pushed yourself up. You feel his hands on your inner thighs, fingers closing in, and then the sensation of his warm tongue feeling like it’s drawing a line right up the middle of you. 

Moaning, you put your fingers in his hair and hold on tight. (Is that why he keeps it long on top?) He puts his hands on the small of your back and raises you up so you’re almost seated, and proceeds to eat you out. You can’t tell if he’s fucking you with his tongue, or if you’re fucking his face. 

Hands still clenched in his hair, you hear yourself murmuring wordlessly. All you can see is the top of his head, his nose, the occasional flash of tongue, and shoulders criss-crossed with scars. You don’t know if you’re having clusters of small orgasms or one huge one, but now it doesn’t matter. You’ve never let yourself go like this before.

You moan and let go of his hair, tapping his head three times without thinking about it. 

He’s sweaty, wet, and laughing again, looking up at you. “Did you just tap out?”

You’re laughing breathlessly with him. “It… it worked, didn’t it?”

He raises up so he’s leaning over you, kissing your mouth that feels bruised already. You grope for his boxer shorts. He’s so hard that you yank them down and they’re caught on it. He pushes them down and guides your hand up the hot, smooth shaft, almost as thick as it is long. “See what you do to me? Those noises you were making? Fuck.”

You push his boxers down to the floor and he steps out of them. You lean forward and cup his balls in your hand, sucking the pre-come off the head of his cock.

You want to see him moaning and flushed, just like he saw you.

“Hey, hey, hey,” he protests, stepping back. “I’m gonna last about two minutes, you do that.”

You sit on the edge of the bed, legs spread, all inhibitions gone. “Then you’d better fuck me.”

Another ear-to-ear grin. He bends down to get his jeans and fishes in one of the pockets. You admire the view, the freckly, thickly-packed, bowlegged view. He’s made of what you call “working muscle”, the kind you can’t get in a gym. His _back muscles_ have back muscles. Facing away from you, he slips the condom on and walks back over. He effortlessly scoops you up the way he had you before, and it’s back to the chair.

“You like this chair,” you tease, wrapping your legs around him. 

He grins crookedly. “I like the view. I like watching your face, Y/N.”

You blush and climb onto his lap. You don’t sit right down on his cock. You take it slow and torturous, letting in just an inch at a time. He groans but he doesn’t stop you, closing his eyes a little each time you take him in. On impulse, you lean down and kiss him. The taste of you and whiskey. He doesn’t shy from it. He returns the kiss eagerly, hands rubbing your back. You don’t think you’ve ever kissed a simple hookup quite so much, or at least not one who enjoyed it this much.

When you finally take in the full length of him, he moans into your mouth, pulling you tighter against him. You pull back to watch his face. Good grief, he’s beautiful, and something about the naked need in his face makes him more beautiful. You playfully dip and rise, tightening your muscles around him. His hands wander your body like you’re art, like he has to touch every inch of you.

His rough palms travel up your thighs, to your stomach, up to your breasts and pause in your hair, on your face. 

His breathing starts to change and you watch him carefully. His shoulders and chest are ruddy with exertion, like he’s holding something at bay. You rise and dip faster, hearing your thighs slap down on his.  
What would make the beautiful man unravel? You squeeze down harder, faster, playing with your breasts so he can see, sucking on your fingers to make them wet. 

He closes his eyes, tongue playing on the back of his teeth. Now he’s fucking up into you, hips meeting your challenge. The sound of your fucking is so loud, the sound of the chair thumping against the floor so loud, you expect a knock on the door at any moment. If you weren’t holding onto him, you’d be on the floor. 

His breathe is ragged now. You lean forward so that your breasts are in his face. You hear a muffled “holy shit, Y/N” and his fingers dig into you, trying to rearrange you just a little, but you’re not budging or slowing down. With his face in your chest, he wraps his arms around your back, fucking you hard enough to leave bruises, panting. 

You run your fingers through his short hair, not trying to match him now as you pull back. He comes _hard_ , fingers digging into your ass like a threat. _Don’t you dare move._ His eyes go distant and his face goes slack. 

You start to get up but he holds you in place. “Don’t… I like… I like it inside.” His heart is beating loud enough for you to hear, and everywhere you touch him, his skin is hot. 

You hold onto him and glance at the trail of destruction around the room so far. Three more condoms are laying on the floor next to his jeans. You laugh and he looks over. 

“Optimistic?” you ask teasingly. 

“Realistic,” he says firmly, his breath starting to go back to normal. He fixes you with a dangerous and playful look. “That was just the warm-up.”


	3. The Wager

**Summary for the Chapter:**

> Dean makes a bet: Whoever begs to fuck first? Gets the prize.

You wake up from a heavy, dreamless sleep to hear the door open and close.

You’re tangled up naked in the sheets, your muscles relaxed, hurting in all the right places. Every part of your bare skin that touches the soft sheets makes you feel like some kind of goddess. 

You turn to where his clothes were left on the floor and see that the jeans and t-shirt are gone. His flannel shirt is still there. You scoop it up and put it on. It’s soft and care-worn, and there’s a hole in the left sleeve the size of your thumb. You go back to the bed feeling sensual, absolutely open wide to him. 

Dean comes back quietly on his bare feet until he sees you’re awake, eyebrows going up at the sight of his flannel shirt around you, kind of stunned. He’s got his arms full of stuff from what looks like a vending machine. “That’s what I get for leavin' my shirt unattended.”

You open the shirt as if examining it, playfully flashing your breasts in the process. “I think it looks better on me, no offense.”

He makes a little choking sound in his throat. “Oh, none taken.”

You don’t realize how thirsty you are until you see the bottle of cold water tucked under his arm. He hands it over and you break the seal, drinking half of it. 

“No room service after eleven,” he says sadly, dumping snacks onto the bed in front of you before sinking into the chair. There’s peanut M&Ms, a plastic sleeve of tiny cinnamon donuts, some chips, a couple of chocolate bars, and an apple danish thing he claims for himself. You laugh and take a chocolate bar, feeling like a little kid on a camping trip with no adult supervision. 

As you eat your candy bar, you let the shirt fall open, exposing your still-reddened nipples. You moan happily as you eat. You draw your knees up toward you but keep your thighs apart, so that you’re on display for him. When you reach over to get more water, you make sure he has an unhindered view of your smooth ass and your still-aching pussy. 

You’re pleased to see him shifting uncomfortably against his tight jeans. 

He narrows his eyes. “Someone besides me’s gettin’ horny again.”

You grin, let the shirt fall all the way open, and spread your knees. _Talk is cheap._

Rising from the chair, he yanks his shirt over his head again. He sweeps all the snacks off the bed except for the cinnamon donuts and shakes them at you. “Alright, how about a wager?”

“I’m listening.”

“I’m not sure you got your six orgasms before.” Dean holds up one hand as you start to protest. “I’m a man of my word, Y/N, and I can’t leave this room without making sure the ratio is met.”

You grin up at him. “I don’t hear a wager yet.”

“Hold your horses, I’m gettin’ there.” He walks over to the belt on the floor and holds it up. “Now, to make sure there’s none of this tapping-out business, I’m gonna belt your hands to the headboard. But…” He unfastens his jeans and carefully pulls them down. There are no boxers underneath. His cock is so hard that it looks painful and strokes his fingers down it, breath hitching just a little. “I’m at a disadvantage. So, whoever begs to fuck first? Gets these donuts.”

“Make it the peanut M&Ms, and you’re on.”

Raising his chin, he drops the donuts in the chair. “A woman of taste. Terms accepted.”

Sportingly, you present him with your wrists. He fastens them to the bars of the headboard, pulling the belt just tight enough to mean business. He gathers all the available pillows, and you realize: he’s done this before. The pillows are to prop you up so your arms aren’t pulled too tight, and they also put you on sexy display at the head of the bed, his flannel shirt falling away from your body. 

He plants his knees on the bed and crawls toward you, bringing his face toward yours. You anticipate a kiss, but instead he whispers softly in your ear, “Tap out with your feet if you need to, but be prepared to kiss those M&Ms goodbye.”

As you laugh, he kisses you, hard and eager, with a promise of teeth in every kiss. You pull at your wrists, wanting to hold his face, to grab onto his hair. 

He laughs into the next kiss. “I don’t know, Y/N, it’s not lookin’ too good for you.”

You kiss him back _hard_ , a little angry now, accusing him in between breaths, “You’re… hustling me… you’ve done this… ohhhh… oh god…” His hard cock drags across your belly, so hot on your skin. “You’ve done this before.”

“Never... said I didn't.” There’s some bite in the kisses now, and an edge to his voice. You feel his sticky pre-come on your belly, you feel the urgency he has for you to give in. “Layin’ here… naked in my shirt… all spread out… fightin’ fuckin’ dirty…”

You hear yourself whimper as he moves down to your breasts, lips and tongue working your sore nipples to little points. Dean doesn’t linger there this time, but leaves them wet, hard, and stiffening in the cool air as he rubs his hands down your belly, down between your knees, then up your thighs, opening you up just a little bit more. 

He grabs your ass in both hands and raises your pussy to his lips, and then… and then he slows down. 

“Oh god,” you rasp. You don’t think you can hold out for six of anything, much less six of this.

He playfully bites and kisses your pussy just like he did your mouth. Only slower. So much slower. You can see every flick of his tongue. As you watch him lick your clit up from under, just as he’d done to your nipples earlier, he watches you back. He watches you as he licks up from your inner thigh and then back up to your pussy. He watches as he slowly fucks you with tongue, pulling it all the way out of you before plunging it in again, closing his eyes just a little, like you’re the best thing he’s ever tasted.

He digs his fingers even harder into your ass, to keep you there as his tongue plunges in and out. You can feel the tip of it searching for the knot of little nerves as he licks into you… closer… deeper…

You make a sound like a strangled sob as you pull futilely at your wrists and thrust your hips up even more. There’s lights behind your eyes, like a fuse just shorted. 

When he comes up for air, his mouth is slick with you. “That’s one.”

You try for a sarcastic remark, but all that comes out is moaning, and all you want to say is _fuck me fuck me fuck me… oh my god, just fuck me…_ The words are playing in your brain like percussion, but you're fighting urgently not to say them.

Then he switches it up, his tongue and its long strokes moving out of you and up to your clit. He frees one hand from your ass to coax your lips apart. His tongue is soft and deliberate now, little circles and soft kisses to tease it out. 

You lose control of your volume. You’re shaking, and sobbing at him. It’s like all your blood and nerves are right under his mouth. You can’t… you can’t… The buckle of the belt rattles against the headboard behind you. “God oh god oh god oh god…”

He raises his face with a hard gleam in his eye. “It’s Dean.” The teasing and kissing becomes more insistent, his tongue a harder point against your clit, faster now, still slow but rhythmic. 

“Faster,” you manage to squeak out. 

He smiles and shakes his head without interrupting his work, and _slows down_ , just the very tip of his tongue slowly tracing a circle around your clit. You’re shaking so hard you might fall apart, and he looks so pleased with himself. His grin and his raised eyebrows. He tongue flicks around and around... holy shit, you're --

“Fuck!” you cry out. Shaking harder with this orgasm than any of the others before it. You can’t hear anything but the blood in your ears. You try to squeeze your thighs together, but his hand and mouth are in the way. 

“That’s two,” he says lazily, infuriatingly calm. “Now, was that a ‘fuck’, or was that a ‘fuck _me_ ’? I got kinda distracted.”

“Fuck _you_ ,” you gasp. 

He laughs, delighted, your insult simply washing over him. “Oh, Y/N, you’re not gonna make it, not with _that_ attitude.”

Now he switches it up again, keeping his tongue flicking at your clit, but maybe a little faster now. But the other hand that was holding your ass is now between your legs. He slips two fingers in and starts roaming with the pad of his fingers… looking for the knot… that hard knot…

The loud sobbing moans are coming out of you again, and you can’t stop them. “Shit… oh… ohhh… _shit_.”

The licking and the sliding in, the soft sucking kisses and his fingers up into you, searching. You part your knees even wider. _Get in there… find me… lick me up… fuck me…_

He’s getting closer to finding that rhythm, the tongue on your hard, sensitive clit syncing up with two… no… three fingers. Three fingers inside you, searching. And he’s there, he’s on it, he’s there, he’s pressing into it…

A loud, moaning cry comes out of you as your raise your hips to his face again. All you can hear is yourself saying “do it, do it, do it, do it.”

Dean licks harder, tongue bearing down, sucking hard. The three fingers fuck in and out, pressing up, pressing there. _Right there._

You’ve got tears running down your face. “If you.. if you stop… I’ll kill… I’ll kill you…” 

He laughs and you feel the vibration of it inside you. He’s a good worker, such a good worker, fingers fucking in and out like a piston, tongue lapping, lips tightening around the clit, sucking at it, just a... just a little. 

The sound that’s wrenched out you probably wakes up the entire floor, but you don’t care. You feel like something’s burst, like your spine is on fire, like every muscle in your body just seized as hard as it could and then went entirely slack. 

He raises up, licks you off his lips and watches you, his eyes hooded and knowing, but his voice comes out scratchy. “I believe that was three.” 

You start desperately pleading with him now. You _beg_ , just like he said you would. “Dean, fuck me, just fuck me, please… _please_ …” 

He pushes your sweaty hair off of your face, planting kisses on your lips that you only just now realize you’ve been biting impatiently. It’s a calming and frustrating gesture at the same time, as you taste yourself on him, your hips involuntary bucking upwards again. 

He holds his cock in one hand, fingers tracing its length, tightening on the shaft, as he finds another of the condoms. He opens it and smooths it on with one hand. With a sly, sleepy grin, he pulls one of the pillows up from behind you, so that it’s between your head and the headboard. 

Kneeling on the bed, he pulls your legs together in front of him and raises your ass off the bed. He locks your knees into place with one arm, rests his head against your calves, and slips into you real slow at first. With more than a little satisfaction, you hear a moan slip out of _him_ for once, as he works his hips. The arm around your knees tightens as he fucks you harder and harder, filling you up. But you can tell from his breathing that he's holding back.

You figure out what the pillow behind your head is for, and fuck into him as hard as you’re getting, knocking the headboard against the wall. You feel his balls against your ass, you feel his short, uneven breaths against your skin. 

You think he can’t fuck you much harder for much longer, but he does, putting his entire body into it. 

You can sense he's trying to control it, but your meeting his thrusts is doing a number on him. Poor, gorgeous bastard. You almost feel bad for him. Almost.

“Y/N…” His voice sound lost and helpless, and with one final thrust, he shudders and comes hard and it seems to ripple throughout him. He can’t hold your legs up anymore, and your knees fall open around him. His chest is flush again, just like before. Sweat’s dripping off him as he leans forward resting his head on your chest. 

You find it an intimate gesture for a hookup, and you rattle the belt buckle against the headboard to remind him. Without pulling out of you, he lazily raises up on one elbow to awkwardly unfasten you. The belt falls down behind the headboard and scrapes the wall on its way down. He makes a dismissive "whatever" gesture and drops his head again. 

Dean sees how red your wrists are and reaches out to take one, to try and sooth your skin with his rough fingers. 

You put a hand on his head to pull him to you. _Lay down._ He pulls out slowly with another hitch of breath, wincing as he straightens his legs, but he rests his head under your breasts, one arm thrown around you in a kind of embrace. It’s weird, but you get the feeling he needs this. You comb your fingers through his damp hair, doing an inventory of the pain: it’s in your shoulders, your wrists, your back, and your hips, the little finger-shaped bruises on your ass where he held on. But _damn_ , it feels good, too. 

You think he’s asleep until he wearily laughs against your skin. "You quit on three!” He laughs harder, like it’s taking his last bit of energy to do it. “Pathetic.” 

If you could move your arm, you would've smacked him on the head. 


	4. The Spoon

**Summary for the Chapter:**

> You're all fucked out, and he wants to go again. Not to worry, he's got you covered.

It’s 2am when you wake up. You reach over to get the last of the water and it wakes Dean, sprawled beside you. He breaks into this sleepy grin when he opens his eyes. You pass him the water and he takes a drink, wiping his mouth with his hand.

You take your place back on the bed tentatively. You’d like to spoon up with him, but it feels weird to… just ask. But as you lay down with your back to him, he moves forward to meet you, cinching you to him with a muscular arm. “You look cold.”

You happily snuggle up to him. His skin feels hot against yours. Just the contact seems like it might be enough to get you going.

“What’s your last name?” you ask, and the minute the words are out of your mouth, you want to take them back. It changes something in the room, something you can’t identify.

He pauses for a few seconds too long, but answers, “Winchester.”

You tell him yours as a sort of conciliatory gesture, but it’s too late: you made it weird.

As if he senses this, and wants to fix it, he brushes his bottom lip back and forth slowly across your ear and says, “My brother and me… we work together. We travel all over, fixing up old cars. Probably leaving town tomorrow after we, uh, settle up on this latest job.”

You want to set him at ease that he doesn’t need to tell you he’s leaving town. He doesn’t need to be worried about you. At the same time, you don’t want to think any further into the future than right now. “Is it the car you stopped at in the parking lot? It’s beautiful.”

Strangely, he gets even warmer when you say this. “No, that’s my car. She’s good advertising, huh?”

“Gorgeous. I can tell you take good care of her.” You cuddle up to him a little more. “That has to be an interesting job. You don’t live anywhere, you just travel?”

“We have a few places we crash for awhile when business is slow.” His fingertips trace a soft line from your shoulder down to the crook of your arm. “We’re used to it, I guess. Dad was a Marine, so we moved around a lot.”

Well, that explains why you couldn’t place his accent to save your life. Also, you had figured _he_ had been in some branch of the service. Something about the way he carries himself. Not formal, just... confidently.

You tell him about your job a little, but it sounds so boring that it makes you self-conscious. You tell him you wish you were closer to your family, something you’d only recently admitted to yourself. It was weird, but he actually seemed interested in your boring life with its day-to-day dysfunction, it’s normalcy, and your trips downtown to lose yourself just for a little while. There was something soft about his voice when he asked, but you couldn’t place it.

Your eyelids start to get heavy when Dean shifts position, and you feel his hard cock pressing into your ass. Exhausted, you laugh. “Are you serious?”

You can hear the grin in his voice. “Shouldn’t’ve wiggled your sweet ass against me, Y/N.”

“I wasn’t wiggling!” You halfheartedly slap at his hand. “I can barely move.”

Dean’s voice is a soft rumble in your ear. “What if I did all the movin’?”

“Hmm?” Something about the combination of his low whiskey voice and the soft strokes he’s painting on your skin has you intrigued, but you’re blissfully sleepy, too.

He digs around next to the bed, and you hear the wrapper being torn from another condom. You feel his hand brush your back as he slips it on. He gathers you to him more insistently, raising your hips so that your ass almost rests on his belly. He sleepily strokes your hip and then your inner thigh, raising your leg up enough to get his knee in between. He brings his hand up to his mouth to wet his fingers, and the sound of that, or maybe just the thought of his sensuous mouth closing on his fingers, makes you wet.

He slicks his fingers against you, laughs at how ready you already are, and arranges himself behind you until his cock slides into you. With one arm braced across your breasts, and the other across your hips, he drags you to him, experimentally shifting downward and out of you, then upward and back in. “Comfortable?”

You shift your hips just a bit to make the angle better, and he slips in deeper. You can’t help but moan. “Yeah, this is… mmm.”

“You ever done this before?”

You shake your head, your mind filled with the sensation of him rocking into you, gently sliding out, just a little, and pushing his hips back up to slip in. You fold your hands under your head, and Dean holds tight, fucking you gentle and slow. You feel like you’re floating.

“You don’t have to do anything,” he whispers. His right palm is lazily stroking your breast, while his left is flat against your belly. His lips brush the back of your neck, trailing soft kisses to the top of your spine.

Dean raises the hand that was on your belly to your lips. “Get ‘em wet. You won’t be sorry.”

Playfully, you suggestively lick and suck them. He tastes like… well, you. He growls but feels even harder inside you.

With the wet fingers, he strokes your pussy and slips three fingers right over your clit, pressing into it, holding you tight to him. You’re confused at first… and then he starts rocking his hips again. Rocking you forward. Rocking your clit against his stiff fingers.

“Friction,” he whispers.

You find yourself rocking slowly with him, breath catching when your clit rubs against his fingers, breath catching again as you shift back and his cock moves in you. It’s somehow the sweetest, dirtiest thing you’ve ever felt.

He leans his head forward on your shoulder. “Don’t rush it. There’s no hurry.”

You clench your pussy down on him in frustration and he laughs, spreading your lips with two fingers so that his middle finger can softly, slowly, stroke your clit.

He brings his fingers up again to your lips. This time you suck them hard, all the way to the last knuckle. Now you hear his breath catch. _Good_.

Just tasting yourself on his fingers, thinking of taking his cock into your mouth, and his cock inside you has you all stirred up again.

He slides his wet fingers out of your mouth, down your breasts, and back to your clit. A little faster now, alternating tight little circles with his fingertips with the palm of his hand. Right up against that hard little nub.

You’re wet, you’re so wet. You can feel his thrusts inside of you quickening. He smears his fingers down in the wet… and pushes his fingers into your open mouth again, giving you a taste of what he’s doing to you, smearing it across your lips.

You bite down now, licking and sucking, raising your leg so you can take him even deeper. _More. Now._

This time, he rubs the hard nub of your clit without mercy, spreading the wetness around. You’re grinding helplessly against his hand while he thrusts harder. If it weren’t for his arm braced hard across your breasts, you feel like you would fall. You push down in to him, begging for it in a whisper. He feels so swollen inside. He’s losing control because you are. _Very good_.

He rearranges you a little, trying to buy time. Shoving his fingers into your mouth again, he loses it. You feel his stomach muscles tense. You feel his balls tighten against you. Thinking of how hard his cock is, you suck his fingers into your mouth. He gasps again, head jerking, a low growl in his throat, and you can’t hold on to it anymore. You pull your knees toward your chest, let his cock slip out, grind on him to push it back in, and come so hard that you feel the wet of it on his thighs. You keep him inside and playfully grind your ass against his balls. He moans so loudly, you think he might’ve sprained something.

Now you’re unbelievably horny and wide awake, and you want him to fuck you again and again and again.

“Stay right where you are,” Dean orders. Like you'd _dream_ of moving.

He pulls his arm and leg out from under you, moves so that he’s at the end of the bed, and pushes his face between your legs, under your sopping pussy, his thumbs holding your lips apart as wide as he can. As you lay face-down on the bed, he eats your pussy like he’s starving. You grind against his mouth, smearing the wet, suffocating him. Just the thought of his tongue, of his pussy-juice covered face, sends you over the edge again. You feel the wet drip down his chin. You raise your hips and grind harder, moaning.

You feel the slickness on his fingers when he digs them into your ass. He circles your clit with the point of his tongue, humming and sucking. It’s too much. Your hips jerk and you’re gone again, tapping out.

“Too much,” you gasp. “Stop. Can’t.”

Dean untangles from your legs to lay beside you and hold you. He kisses your neck and your shoulders while you shake.


End file.
